Old World Third Street
The entrance to Buckhead Saloon (1044 N. Old World Third St.) is as bare-bones as you can get—just a brick wall with a dimly lit red sign that, on a passing glance, wouldn't suggest anything worthwhile is inside. But as they say, don't judge a bar by its façade, because Buckhead's is one of the niftier hot spots in town, and certainly the bread and butter of Old World Third. The monstrous bar looks like an oversized, tricked-out lodge, filled with antlers and mounted stags. For a more social drinking experience, try one of the cool beer towers.
Across the street from Buckhead's are the white-and-red-striped awnings of Buck Bradley's (1019 N. Old World Third St.), sort of the ying to Buckhead's yang. Stop in here for some quality grub before or after a Bucks game or concert and stick around to shoot some pool in the upstairs game room. The restaurant also has one of the longest bars you're likely to see, stretching nearly from wall to wall—for the impatient drinkers out there, that means complete beverage optimization.
If you haven't been to Munich in a while or simply like drinking out of a gigantic stein, check out Old German Beer Hall (1009 N. Old World Third St.), a narrow, perpetually packed taste of the Old Country. OGBH, as it's affectionately called by the college kids who frequent it, is a loud, sweaty, shoulder-to-shoulder blast from the past—the ideal rendezvous point toward the end of an already crazy night. What's more, it's the only bar in Milwaukee where dancing on tables is truly encouraged.
There are some good Italian restaurants in Milwaukee, and then there's the Calderone Club (842 N. Old World Third St.), an upscale “Sopranos”-type joint with pizza and pasta too good to refuse. The dimly lit, easygoing spot finds a way to be both elegant and casual, which lends itself perfectly to romantic dates or fine-dining experiences with a pack of friends. Then you throw in the buttery calamari and fully loaded bar? Fuggedaboutit.